This invention covers the use of 1(3H)-isobenzofuranone defined according to the structure: ##STR2## in augmenting, enhancing or imparting aromas in or to perfume compositions, colognes or perfumed articles.
The compound having the structure: ##STR3## is a known compound. However, its use in perfumery is unknown. Benzofuranone type derivatives, e.g., coumarin, defined according to the structure: ##STR4## and dihydrocoumarin having the structure: ##STR5## are known in perfumery and their perfumery properties are described by Arctander, "Perfume and Flavor Chemicals (Aroma Chemicals)", Volume I, published by the author in 1969 at monographs 704 and 934. Furthermore, diethyl phthalate having the structure: ##STR6## is also known for its use in perfumery as shown by Arctander at monograph 913.
Sweet coumarin-like aromas with almond-like, sweet, hay and heleotropin-like topnotes are highly desirable in the field of perfumery. The prior art does not disclose, expressly or implicitly, the use of the compound having the structure: ##STR7## or the creation of the combination of perfumery notes which are not only substantive but powerful as well.
The compound having the structure: ##STR8## is known as "Phthalide" and is distributed by the Sigma Aldrich Company of 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233. It is listed in the Sigma Aldrich catalog as No. P3960-5 and indicated to have a melting point of 72.degree.-74.degree. C. and a boiling point of 290.degree. C. The synthesis of phthalide is set forth by Chaikin and Brown, "Reduction of Aldehydes, Ketones and Acid Chlorides by Sodium Borohydride" in Volume 71, J. Am. Chem. Soc., January 1949 at pages 122-125.
The syntheses and properties of phthalide having the structure: ##STR9## are also set forth in Beilstein [System No. 2463] XVII, 310-311 at pages 161 and 162 and at Beilstein [System No. 4948] E III/IV 17 (ES10).
Isomeric homologs of pthalide are known for use in perfumery, having the structure: ##STR10## Thus, the genus defined according to the structure is disclosed in European Published Application No. 707,575 as well as PCT Application No. 95/30667, abstracted by DERWENT CHEMICAL PATENTS INDEX ALERTING ABSTRACTS BULLETIN, issued Jun. 14, 1996 as follows: FIRM E1396-010568/01=EP 707575A1 Use of dihydro-benzofuranone derivs. as perfuming ingredients--specific claimed cpds., prepn. and compsns. (Frn)
FIRMENICH SA 94.05.09 94CH-001441 PA1 D23 P34 (D21 D25) (96.04.24) *WO 9530667-A1 C07D 307/83, PA1 A61K 7/32, C07D 307/92, A61L 9/01 PA1 95.03.27 95EP-911475 95.03.27 95WO-IB00206 Based on WO9530667-A (Eng) R(CH DE FR GB LI NL)
A dihydrobenzofuranone cpd. of formula (I) is used as a perfuming ingredient, R.sub.1 -R.sub.4 =H, 1-5C (un)satd. alkyl, 1-4C alkoxy, 5-6C cycloaliphatic or aromatic gp., with the cyclic gp. opt. substd. with 1 or more lower alkyl; or 2 adjacent R gps. together form a 5-6C (un)satd. ring, opt. substd. by 1 or more lower alkyl; and the other 2 gps.=H.
Use--Perfumed articles include toilet waters, soaps, bath or shower gels, shampoos or other hair prods., cosmetics, deodorants for the body or the air, detergents, textile softeners, and prods. for upkeep. Use of 10 cpds. is claimed, esp. 3,4,6-tirmethyl-2H-benzo(b)furan-2-one, 3,6,7-trimethyl-3H-benzo(b)furan-2-one, 3,5,6,7-tetrahydro-3-methyl-indeno(5,6-b)furan-2-one 5,7-diisopropyl-3-methyl-3H-benzo(b)furan-2-one (II) or 5,7-di-tert.-butyl-3-methyl-3H-benzo(b)furan-2-one or a mixt. of (II) and 3-methyl-cyclopentadec-5-en-1-one.
ADVANTAGE--The cpds. impart a lactone, coumarin, fruity or musky note. (Dwg.No.0/0)
CT: 3.Jnl.Ref EPO41122 U.S. Pat. No. 4,252,817 WO9412143 ##STR11## Thus, in the structure: ##STR12## R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen or C.sub.1 -C.sub.5 saturated or unsaturated alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.5 -C.sub.6 cycloaliphatic, or aromatic with the cyclic group optionally substituted with one or more lower alkyl; or two adjacent R groups together form a C.sub.5 -C.sub.6 saturated or unsaturated ring optionally substituted by one or more lower alkyl groups with the other two groups being hydrogen.
However, the genus of compounds having the structure: ##STR13## is different in kind rather than degree from the structure of pthalide, to wit: ##STR14##
Nothing in the prior art discloses or implies that the compound having the structure: ##STR15## is useful in the field of perfumery. The compound having the structure: ##STR16## has unobvious, unexpected and advantageous properties over any compounds having related structures existing in the prior art.